Sodium hydride → (2E)-3-(2-ethyl-2H-indazol-4-yl)acrylonitrile

HRID 1639772Notes

Reaction equation

[C:1]([CH2:3]P(=O)(OCC)OCC)#[N:2].[H-].[Na+].[CH2:14]([N:16]1[CH:24]=[C:23]2[C:18]([CH:19]=[CH:20][CH:21]=[C:22]2[CH:25]=O)=[N:17]1)[CH3:15]>O1CCCC1.[Cl-].[NH4+]>[CH2:14]([N:16]1[CH:24]=[C:23]2[C:18]([CH:19]=[CH:20][CH:21]=[C:22]2/[CH:25]=[CH:3]/[C:1]#[N:2])=[N:17]1)[CH3:15]

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of diethyl cyanomethylphosphonate (254 μL, 1.57 mmol) in tetrahydrofuran (6 mL) was added 60% sodium hydride (57.9 mg, 1.45 mmol) under ice-cooling, and the mixture was stirred at 0° C. for 15 min. To the mixture was added a solution of 2-ethyl-2H-indazole-4-carbaldehyde (210 mg, 1.20 mmol) in tetrahydrofuran (6 mL) under ice-cooling, and the mixture was stirred under ice-cooling for 15 min. The reaction solution was diluted with saturated aqueous ammonium chloride solution, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, and dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane=15/85→50/50) to give the title compound (222 mg, yield 93%).

Workup

temperaturecooling
temperaturecooling
stirringthe mixture was stirred under ice-
temperaturecooling for 15 min
extractionthe mixture was extracted with ethyl acetate
washThe extract was washed with saturated brine
dry with materialdried over anhydrous sodium sulfate
customthe solvent was evaporated under reduced pressure
customThe residue was purified by silica gel column chromatography (ethyl acetate/hexane=15/85→50/50)

Sources & evidence

ORD record: ord-bcbade188e9f45198606bf614c8ae2bf
Source dataset: uspto-grants-2012_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08110585B2

Reaction notes

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